Founders Talk: Startups & Leadership

Founders Talk: Startups & Leadership
In-depth, one-on-one conversations with founders, CEOs, and makers. The journey, lessons learned, and the struggles. Let’s do this! Host Adam Stacoviak dives deep into the trials, tribulations, successes, and failures of industry leading entrepreneurs, leaders, innovators, and visionaries.

Slow and steady wins
Aug 3 • 72 min
Jeff Sheldon is the founder and creator of Ugmonk. Jeff is a designer by trade, and an entrepreneur by accident. I been following Jeff’s journey for the better part of Ugmonk’s existence. I’m also a customer. Jeff and I hold several similar values near…
From acquisition to full conviction
Jul 3 • 91 min
Guy Podjarny is the Founder of Snyk, a security platform that empowers software-driven businesses to develop fast and stay secure. Prior to Snyk, Guy founded Blaze which was acquired by Akamai and became CTO. We talked through the topic of acquisition —…
Leading GitLab to $100M ARR
Jun 9 • 61 min
Sid Sijbrandij is the Co-founder and CEO of GitLab — an all-remote company and complete DevOps platform. As a company, they have their eyes set on taking the company public to IPO and they’re very outspoken about their culture, open handbook, and how they…
Building a real programmable robot
May 8 • 77 min
The role of a father plays a pivotal role in a child’s life. Ian Bernstein is a former Founder of Sphero and is now the Founder and Head of Product of Misty Robotics — they’re building the first programmable robot for the home and business. It’s called…
Becoming an accidental founder
Jan 24 • 41 min
Mike McDerment is the founder and CEO of FreshBooks. Believe it or not, Mike became a founder by accident. Like many of us, Mike had an itch that he just had to scratch. One thing led to another and soon enough FreshBooks became a key tool in the belt of…
Mastering the art of quitting
Jul 5, 2019 • 98 min
Lynne Tye is the founder of Key Values, a platform where developers find engineering teams that share their values. To be more precise, Lynne is a solo-founder. She’s also a team of one. Lynne’s path to becoming a founder was anything but typical. She had…
Failing to build a billion-dollar company
Jun 14, 2019 • 72 min
Sahil Lavingia is the founder and CEO of Gumroad, a platform for creators to sell the things they make. Since 2011 Gumroad has sent over $200 million dollars to creators. That’s a big number. Sahil’s ambitions lead him to believe that Gumroad would become…
What are you optimizing for?
May 31, 2019 • 73 min
Saron Yitbarek is the founder and CEO of CodeNewbie — one of the most supportive community of programmers and people learning to code. Saron hosts the CodeNewbie podcast, Command Line Heroes from Red Hat, and she’s also the creator of Codeland Conference…
Building a hardware/software product company
May 23, 2019 • 66 min
Colin Billings is the founder and CEO of Orro where they’ve built the first truly intelligent home lighting system. It knows when you’re in the room, and adjusts the lights automatically for you. But Colin’s path to starting this company wasn’t a straight…
Zero up-front costs for a CS education
Apr 19, 2019 • 45 min
What would be the impact on the world if a Computer Science education was available to you completely free of charge until you get a job in that field paying $50,000 or more? That’s the question that drives Austen Allred and the team behind Lambda School.…
Isaac Schlueter on building npm and hiring a CEO
Jan 25, 2019 • 68 min
With JavaScript in every corner of software development and npm in every corner right along with it, the rise of npm can be drawn as a hockey stick up and to the right with Isaac Schlueter at the top grinning ear to ear. After reading their recent…
Leading data-driven software teams and products
Dec 21, 2018 • 88 min
For the final show of 2018 I’m talking with Travis Kimmel, the CEO of GitPrime. Travis has spent years as an engineering manager. Travis’s mission at GitPrime is to bring crystal clear visibility into the software development process and bridge the…
How $3.8M in seed funding started Gatsby as an open source company
Nov 30, 2018 • 72 min
Kyle Mathews is the founder and CEO of Gatsby, a new company he’s building around an open source project of the same name. Gatsby as a project describes itself as a flexible modern website framework and blazing fast static site generator for React.js. At…
Tidelift’s mission is to pay open source maintainers
Sep 21, 2018 • 68 min
Donald Fischer and the team at Tidelift are on a mission of making open source work better — for everyone. To pay the maintainers of open source software they are putting a new spin on a highly successful business model that’s a win-win for the…
From dropout to CEO of Sentry and taking on New Relic
Sep 16, 2018 • 72 min
David Cramer dropped out of high school AND college, but that didn’t stop him. He ended up teaching himself programming and eventually landed his first job as the webmaster of a World of Warcraft community website. What a beginning… We talked through “the…
BONUS: Growing a successful sales team at Sentry
Sep 14, 2018 • 10 min
Here’s a bonus segment from episode #57 of Founders Talk with David Cramer, co-founder and CEO of Sentry. Check the feed for the full length episode (later today). We talked about sales in the full length episode, but this BONUS segment is a completely…
Eric Berry is funding open source with CodeFund
Aug 28, 2018 • 81 min
Eric Berry started Code Sponsor a year ago because of his passion for finding ways to sustain and fund open source developers. He ultimately had to shutdown due to potential legal issues with GitHub, but was given new life as CodeFund when he went to work…
Side hustle to $35M ARR at Zapier
Aug 17, 2018 • 69 min
Bryan Helmig, Wade Foster, and Mike Knoop started Zapier in 2011 as a side hustle. They ultimately applied to Y Combinator, twice. And this year they hit $35 Million dollars in annual revenue. I talked with Bryan Helmig (CTO) through the backstory of…
From side project to $7.25M for Unsplash
Jul 6, 2018 • 80 min
When Mikael Cho started Unsplash from its small beginning as a Tumblr blog and side project, he had no idea it would have such a huge impact and ultimately disrupt the photography industry. In this episode, Mikael shares the backstory of Unsplash, how it…
Starting over from zero
Jun 28, 2018 • 57 min
Danielle Morrill joined the show to talk about how she’s starting over from zero after the recent acquisition of Mattermark to FullContact where she held the role of CEO and co-founder who walked away with “zero dollars and a job”. We talked through the…
Growing Open Collective
Jun 15, 2018 • 71 min
Pia Mancini joined the show for the first episode back from a nearly 5 year hiatus. We talked about her work at DemocracyEarth, being a mother, her new role as CEO of Open Collective, their focus, supporting ad-hoc community formation all around the…
🔥 Founders Talk is back!
Jun 15, 2018 • 3 min
It’s been just shy of 5 years since I’ve published a new episode to this podcast. The break was planned actually. Long story short, I had to focus. If you want to hear the slightly longer explanation, you should listen.
Sam Soffes / Onward
Sep 11, 2013 • 78 min
Could this be Sam’s final appearance on Founders Talk? Only time will tell. Sam says he’s moving onward. New things await. The future is bright and he’s wearing shades. Follow along.
Chad Pytel / thoughtbot
Aug 20, 2013 • 97 min
Adam talks with Chad Pytel, founder of thoughtbot.
Geoffrey Grosenbach / PeepCode, Part 2
Aug 19, 2013 • 68 min
Adam talks with Geoffrey Grosenbach, founder of PeepCode and now the VP of Open Source at Pluralsight.
Kevin Delaney / Charity Hack
Jul 22, 2013 • 62 min
Adam talks with Kevin Delaney, the founder of Charity Hack - a simple concept that takes 5 amazing charities and the most talented people you can find to create innovative fundraising campaigns for those charities.
Tim Smith / The East Wing
Jun 27, 2013 • 86 min
Adam talks with Tim Smith, the creator of The East Wing, Tim Likes to Teach, Lustra and more. Tim is a master of the art of design and UX and loves hacking on front-end web codes.
Drew Strojny / Memberful
Jun 13, 2013 • 60 min
Adam talks with Drew Strojny the founder of The Theme Foundry and Memberful. Drew is back again to talk about his latest product, Memberful - a membership as a service site that lets you create a membership in minutes and start selling monthly or yearly…
Dalton Caldwell / - Part 2
Jun 7, 2013 • 94 min
Adam talks with Dalton Caldwell the Founder of Since we barely scratched the surface of the planned conversation around what he’s doing with in part 1, Dalton agreed to come back on the show for a part 2 to discuss the back story of…
Robert Sha / CAPSULE + Minimalist
May 30, 2013 • 107 min
Adam talks with Robert Sha, the founder of CAPSULE and the maker of Minimalist - a super slim wallet for minimalists popularized by its successful project on Kickstarter.
Daniel Genser & Jamie Smyth / TypeEngine
May 23, 2013 • 95 min
Adam talks with Daniel Genser and Jamie Smyth, the makers of TypeEngine, to talk about their “beautifully simple” solution to publishing a magazine to Newsstand and the future and democratization of digital publishing.
After Founders Talk #42
May 16, 2013 • 4 min
Adam Stacoviak talks with Dalton Caldwell the Founder of after Founders Talk #42.
Dalton Caldwell / - Part 1
May 16, 2013 • 55 min
Adam talks with Dalton Caldwell the Founder of This is a hefty part 1, mainly focusing on the road traveled by Dalton to get to We barely scratched the surface of the planned conversation around what he’s doing with We end this…
Garrett Dimon / Sifter
May 10, 2013 • 100 min
Garrett Dimon the Founder of Sifter and writer of Starting + Sustaining joins Adam to share his history with becoming a founder and the wisdom he’s gained by bloodying his knuckles over the years with lessons learned.
Sam Soffes / Seesaw - Part 3
Dec 6, 2012 • 89 min
Sam Soffes the Founder of Nothing Magical and NOW the VP of Engineering at Seesaw joins Adam Stacoviak to share some of the most recent details and changes for him in the finale part 3 show. Core take away? Embrace risk. Stay focused.
After Founders Talk #39
Aug 7, 2012 • 8 min
Adam and guest Sam Soffes the Founder of Nothing Magical and the maker of Cheddar after Founders Talk #39.
Sam Soffes / Nothing Magical, Cheddar - Part 2
Aug 7, 2012 • 91 min
Sam Soffes the Founder of Nothing Magical and the maker of Cheddar joins Adam Stacoviak to share more details about the rise of Cheddar, its revenue, metrics, numbers and more. Sam shares lessons learned, his dreams as well as his thoughts on those who…
Sam Soffes / Nothing Magical, Cheddar - Part 1
Jul 13, 2012 • 100 min
Sam Soffes the Founder of Nothing Magical and the maker of Cheddar joins Adam Stacoviak to share all the details of his wild ride as an indie software developer and designer. Sam has worked at Hipstamatic, built YouTube ripoffs, gotten offers from some of…
After Founders Talk #37
Jul 5, 2012 • 24 min
Adam and guest Sarah Hatter the founder of CoSupport after Founders Talk #37.
Sarah Hatter / CoSupport - Part 2
Jul 5, 2012 • 88 min
Sarah Hatter the Founder of CoSupport, joins Adam for part 2 of 2 to go back in time and dig deep into her history, we learn about “the early days” and how she got started, her passions for TV and her podcast TVBFF, the early days of blogging and…
After Founders Talk #36
Jun 28, 2012 • 17 min
Adam and guest Sarah Hatter the founder of CoSupport after Founders Talk #36.
Sarah Hatter / CoSupport - Part 1
Jun 28, 2012 • 63 min
Sarah Hatter the Founder of CoSupport, joins Adam for part 1 of 2 to share her passion for great customer support for web products, being a woman in a man filled industry, her thoughts and history with potentially selling her company and getting…
After Founders Talk #35
Apr 11, 2012 • 7 min
Adam Stacoviak and guest Steve Espinosa after Founders Talk #35.
Steve Espinosa / AppStack
Apr 11, 2012 • 60 min
Steve Espinosa, the Founder of AppStack, joins Adam to tell his story of hustling his way to the top, gaining the trust and friendship of Jason Calacanis, Dave McClure, Eric Schmidt and the awesome team behind Google Ventures, what it means to focus and…
After Founders Talk #34
Apr 3, 2012 • 6 min
Adam Stacoviak and guest Jon Crawford of Storenvy after Founders Talk #34.
Jon Crawford / Storenvy
Apr 3, 2012 • 56 min
Jon Crawford, the Founder of Storenvy joins Adam to talk about how everything began for Storenvy, his road from Kansas to Austin, TX to SF, how he got kicked out of Y Combinator the same week he was accepted then raised $1.5M for Storenvy, and how he’s…
After Founders Talk #33
Mar 2, 2012 • 9 min
Adam Stacoviak, Nate Peretic & Jay Fanelli after Founders Talk #33.
Nate & Jay / United Pixelworkers
Mar 2, 2012 • 86 min
Nate Peretic & Jay Fanelli, the Founders of Full Stop and United Pixelworkers join Adam to talk about plotting and planning to leave old jobs, being outspoken and opinionated, having a core set of principles and not deviating from them, reaching out to…
Nathan Ryan / Proxart
Feb 21, 2012 • 68 min
Nathan Ryan, the Co-founder of Proxart joins Adam to talk about what to do when you’re bored in Santa Clarita, team development, keeping everyone motivated and on track, and his globalized local focus on art and how artists relate to, react to, and change…
Kyle Bragger / Forrst
Feb 10, 2012 • 79 min
Kyle Bragger, the Founder of Forrst joins Adam to talk about how everything got started for him, how he met Gary Vaynerchuk - which ultimately led Gary and his brother Aj to provide the initial angel funding that helped Kyle work full-time on Forrst. Kyle…
Peter Cooper / Cooper Press
Feb 2, 2012 • 89 min
Peter Cooper, the Founder of Cooper Press joins Adam to talk about all the stops along the way on his path to where he is today. Peter shares an immense amount of knowledge on tech publishing, what he’s learned about marketing, email newsletters done…
Francisco Dao / 50 Kings
Jan 25, 2012 • 79 min
Francisco Dao, the Founder of 50 Kings (an invitation-only, private community of thinkers and doers) joins Adam to talk about the importance of building relationships, doing only what interests you, entrepreneurship, all sorts of “insider” knowledge…
Andrew Wilkinson / MetaLab
Jan 13, 2012 • 62 min
Andrew Wilkinson, the Founder of MetaLab (an interface design studio) joins Adam to talk about how he started as a one-man band and learned to delegate to succeed. Andrew started MetaLab in 2006 and quickly built the company into a multi-million dollar…
Ryan Carson / Carsonified
Dec 21, 2011 • 46 min
Ryan Carson, the Founder of Carsonified and Treehouse, joins Adam to talk about all the details of starting his new venture, Treehouse.
Bryan Zmijewski / ZURB
Dec 9, 2011 • 54 min
Bryan Zmijewski (Shme-yes-key), Founder and Chief Instigator of ZURB, joins Adam to talk about his path to starting ZURB, what sharing code and design patterns has done for their business, product, culture and team development, and what it takes to make…
Dan Martell / Clarity
Nov 30, 2011 • 53 min
Dan Martell, Co-Founder of Flowtown, joins Adam to talk about his road to success with Flowtown, getting acquired, how he met his Co-Founder Ethan Bloch on Twitter, angel investing and being an advisor, giving back to charity and customer development and…
Dan Cederholm and Rich Thornett / Dribbble
Nov 10, 2011 • 70 min
The founders of Dribbble, Rich Thornett and Dan Cederholm, join Adam to talk about how Dribbble came to be, the 3rd edition of Bullet Proof Web Design, product development, new and existing features of Dribbble as well as focusing on revenue producing…
Vitaly Friedman / Smashing Magazine
Oct 26, 2011 • 63 min
Vitaly Friedman, Founder of Smashing Magazine, joins Adam to talk about the beginnings of Smashing Magazine, taking chances, not being copyable, experimenting to find what works, supporting the community, developing content, paying writers, developing…
Drew Strojny / The Theme Foundry
Oct 22, 2011 • 52 min
Drew Strojny joins Adam to talk about his path in life, playing in the NFL, marrying your business partner, web design and pursuing the unknown, developing digital products and themes for WordPress and the 5by5 logo.
Mark Jardine and Paul Haddad / Tapbots
Sep 30, 2011 • 36 min
Mark Jardine and Paul Haddad join Adam to talk about Tapbots, their side project turned business, designing and developing mobile applications on iOS, establishing and building trust and much more.
Drew Wilson / Valio - Part 2
Sep 22, 2011 • 49 min
Drew Wilson joins Adam again for part 2, to talk about his latest venture, Valio Con, his ad network Yoggrt (sold) and some future products.
Drew Wilson / Valio - Part 1
Sep 15, 2011 • 56 min
Drew Wilson joins Adam for part 1 to talk about his journey as an entrepreneur, the lows, the highs and the in-betweens. Drew talks with Adam about digital projects, how to chase your dreams and more.
Matt Mickiewicz / 99 Designs
Jun 2, 2011 • 44 min
Matt Mickiewicz, Co-Founder of SitePoint, 99 Designs, and Flippa talks with Adam about becoming an entrepreneur at a young age, building marketplaces, finding talented people, and using community development and a forum as the spring board for 99 Designs…
Niel Robertson / Trada
May 28, 2011 • 49 min
Niel Robertson, Founder and CEO of Trada, talks about crowd-sourcing, crowd mechanics, leveraging “the stealth mode”, raising 52 million dollars, community engagement, as well as thoughts on whether or not crowd-sourcing commoditizes freelance expertise.
Avner Ronen / Boxee
May 17, 2011 • 32 min
Avner Ronen talks about his vision of the “Future of TV,” the role Boxee plays in today’s internet video/audio content on the big screen, the backlash of “big media” against Boxee and how they’ve changed their tune and much more.
Noah Kagan / App Sumo
May 12, 2011 • 60 min
Noah Kagan, Founder of App Sumo talks with Adam about his journey to success. Send an email to for more details about something special for 5by5 listeners.
Bill Boebel / Rackspace
May 11, 2011 • 38 min
Adam talks with Bill Boebel, VP Strategy/Corp Dev at Rackspace and Founder of about staying the course, keeping the team motivated during turbulent “cash strapped” times, getting acquired by Rackspace and staying on to continue building the…
Chris Nagele / Wildbit
Apr 28, 2011 • 49 min
Adam talks with Chris Nagele, Founder of Wildbit about his 11 year journey of building Wildbit and ultimately some awesome web products like Beanstalk, Postmark, and Newsberry.
Eric Kuhn / Founders Card
Feb 24, 2011 • 40 min
Adam talks with Eric Kuhn, Founder of Founders Card about the ups and downs of building an online business during the era of the “dot com” bubble, managing hyper growth, getting listed and de-listed on the NASDAQ and building an exclusive benefits…
Rick Perreault / Unbounce
Jan 28, 2011 • 51 min
Adam talks with Rick Perreault, Co-Founder & CEO of Unbounce about entrepreneurship and solving your own pain, sticking to an MVP (Minimal Viable Product) launch strategy, becoming an authority by blogging/marketing before you launch, listening to…
Ryan Holmes / HootSuite
Jan 22, 2011 • 38 min
Adam talks with Ryan Holmes, Founder of Hootsuite entrepreneurship, establishing and leveraging their relationship with Twitter, from “free” to “freemium” with a plan, and growing to well over 1 Million users in 2 years.
Maciej Ceglowski / Pinboard
Jan 10, 2011 • 37 min
Adam talks with Maciej Ceglowski, Founder of Pinboard about turning this side project into the next Delicious, handling a massive in-flux of Delicious users when they announced its “sunset”, keeping the technology and architecture simple and more.
Alex Hillman / Indy Hall
Dec 24, 2010 • 55 min
Adam talks with Alex Hillman, Co-Founder of Indy Hall and co-conspirator/creator of many things, about all things Coworking, people helping people, how to hustle, get unstuck and more. Alex also mentions something “super secret” that’s sure to please.…
Henk Rogers / The Tetris Company
Dec 21, 2010 • 49 min
Adam talks with Henk Rogers, Founder of The Tetris Company, Blue Planet Software and Blue Planet Foundation about the beginnings of and the evolution of Tetris, over-coming brick walls, social and mobile gaming, never giving up, changing the world,…
Amy Hoy and Thomas Fuchs / Slash7
Dec 17, 2010 • 48 min
Adam talks with Amy Hoy and Thomas Fuchs, Founders of Slash7 about product development, profiting from Open Source, the key to happiness, living a Unicorn-Free lifestyle and how Amy and Thomas met and ultimately fell in love.
Allan Branch and Steven Bristol / Less Everything
Dec 7, 2010 • 52 min
Adam talks with Allan Branch and Steven Bristol, Founders of Less Everything about how things got started, why they hate QuickBooks, what it takes to create a successful partnership and more.
Ryan Carson / Carsonified
Nov 30, 2010 • 31 min
Adam talks with Ryan Carson, Founder of Carsonified about the “lessons learned” in creating their latest product, Think Vitamin Membership - the biggest being the need to rename the product and go through a re-branding process. In Q2 of 2011 Think Vitamin…
Lance Jones and Joanna Wiebe / Page 99 Test
Oct 22, 2010 • 39 min
Adam talks with Lance Jones and Joanna Wiebe, Founders of People in bookstores often read page 99 of a book to get a taste for the writing - to determine if they’d buy the book. Lance, Joanna and technical Co-Founder, Steven Luke took that…
Ted Roden / Fancy Hands
Oct 16, 2010 • 56 min
Adam talks with Ted Roden, Founder of Fancy Hands, a team of personal assistants in the cloud ready to work for you right now. For those of you who have an over flowing todo list, get back to focusing on what’s important and give Fancy Hands a try.
Geoffrey Grosenbach / PeepCode
Oct 6, 2010 • 36 min
Adam talks with Geoffrey Grosenbach about his quest for greatness as Senior Visionary in building PeepCode Screencasts. Complete with the signature voice that Geoff delivers, he walks us through the various aspects of building Peepcode from scratch,…